Triethylamine → HCID 10202537, compound

HRID 47668Notes

Reaction equation

HRID 47668 reaction equation
I[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][C@@H:7]([CH2:12][NH:13][C:14](=[O:23])[O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:6][CH2:5]2.C(N(CC)CC)C.[C:31]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])(=[O:34])[CH:32]=[CH2:33]>C(#N)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:16]([O:15][C:14]([NH:13][CH2:12][C@H:7]1[CH2:6][CH2:5][C:4]2[C:9](=[CH:10][CH:11]=[C:2](/[CH:33]=[CH:32]/[C:31]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH:3]=2)[O:8]1)=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 15458tert-Butyl acrylateHCID 10159298benzyl [(2R)-6-iodo-3,4-dihydro-2H-chromen-2-yl]methylcarbamate

Product 1

HCID 10202537HCID 10202537, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6342AcetonitrileSolvent

Procedure

Palladium acetate (224 mg, 1 mmol) was added to a mixture of the carbamate of Example 11 (4.2 g, 10 mmol), triethylamine (2.1 mL, 15 mmol), and t-butyl acrylate (1.76 mL, 12 mmol) in acetonitrile (50 mL) previously degassed with argon for 20 minutes. The resulting mixture was heated at gentle reflux for 26 hours. It was cooled to room temperature. The catalyst was removed by filtration. The filtrate was concentrated in vacuo. The residue was dissolved in ethyl acetate (50 mL), washed with water (50 mL), brine (50 mL), dried over anhydrous sodium sulfate, and filtered over a pad of silica gel. Removal of solvent in vacuo afforded the product as an oil (4.0 g, 95%): 1H NMR (CDCl3) δ1.50 (s, 9H), 1.70 1.85 (m, 1H), 200 (m, 1H), 2.80 (m, 2H), 3.40(m, 1H), 3.65 (m, 1H), 5.12 (s, 2H), 5.25 (m, 1H), 6.21 (d, J=15.3 Hz,1H), 6.76 (d, J=8.4 Hz, 1H), 7.20-7.40 (m, 7H), 7.49 (d, J=15.9 Hz, 1H); CI-MS m/z 424 (M+H+).

Workup

  1. custompreviously degassed with argon for 20 minutes
  2. temperatureThe resulting mixture was heated
  3. temperatureat gentle reflux for 26 hours
  4. customThe catalyst was removed by filtration
  5. concentrationThe filtrate was concentrated in vacuo
  6. dissolutionThe residue was dissolved in ethyl acetate (50 mL)
  7. washwashed with water (50 mL), brine (50 mL)
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationfiltered over a pad of silica gel
  10. customRemoval of solvent in vacuo

Sources & evidence

ORD record
ord-edbc0247ce97492fa9b40e27db6a888a
Source dataset
uspto-grants-2004_03
Patent number
US06699860B2

Reaction notes

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